Syphilis, a known sexually transmitted disease, emerged in new non-venereal forms in the nineteenth century with an ability to reach every remote corner. Through an innocent touch in a barber shop or a pleasing puff at the tip of a narghile, it was only a matter of moment to transmit the disease. As opposed to other fatal diseases such as cholera and plague, syphilis followed long term stages to take over the human body. Hence, it neither manifested itself nor killed its victim suddenly. Furthermore, syphilis was hard to diagnose for syphilis bacteria had the ability of mimicking other internal diseases; therefore, malpractice was very common. Yet syphilis was not only a perplexing medical question but also a significant source of social anxiety among the Ottoman public, causing shame and fear. Syphilis along with other venereal diseases became an alarming issue for the Ottomans following the Russo-Ottoman War of 1877-78, at the end of which most of the territories in the Balkans and Caucasia were lost, and many immigrants and refugees, some of them possibly carrying the disease, arrived in Anatolia. In addition, the increase in the migration of seasonal workers from rural to urban centers as well as from neighboring countries accelerated the spread of syphilis to new regions. By the end of the century, it would have been common for one to encounter syphilis at varying rates in any Ottoman province. This paper explores the impact of governing concern of the medical and political circles over syphilis particularly among male population that became the primary target of the prevention measures during the outbreak of syphilis. Male population was by far the most mobile segment of the Ottoman society for they served in the army as soldiers, worked as seasonal workers and travelled as merchants. Often times sharing homosocial spaces such as coffeehouses, public baths, and bachelor houses, male population became both the target and the medium of syphilis. Analyzing the health regulations for the elimination of syphilis, manuals for the soldiers and self-help books for general readership published by pioneering gynecologists, this paper will address the efforts of Ottoman medical authorities to prioritize the surveillance of male population that contributed to the emergence of new and medicalized discourse and practices regarding masculinity in the late Ottoman Empire.